ChemicalBook CAS DataBase List 2-(Trifluoromethyl)isonicotinic acid

2-(Trifluoromethyl)isonicotinic acid synthesis

12synthesis methods

Product Name:2-(Trifluoromethyl)isonicotinic acid
CAS Number:131747-41-6
Molecular formula:C7H4F3NO2
Molecular Weight:191.11

201230-82-2 Synthesis

201230-82-2
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590371-73-6 Synthesis

590371-73-6
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131747-41-6
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Yield:131747-41-6 146 mg

Reaction Conditions:

Stage #1:carbon monoxide;2-(trifluoromethyl)pyridine-4-iodide with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;sodium hydrogencarbonate in tetrahydrofuran at 120; under 52505.3 Torr; for 20 h;
Stage #2: with hydrogenchloride;water in water at 20; for 1 h;

Steps:

9 Example 9 Preparation of 2-Trifluoromethyl-isonicotinic acid from 4-Chloro-2-trifluoromethyl pyridine
Example 9 Preparation of 2-Trifluoromethyl-isonicotinic acid from 4-Chloro-2-trifluoromethyl pyridine A mixture of 182 mg (1.0 mmol) 4-Chloro-2-trifluoromethyl pyridine, 18.0 mg PdCl₂(dppp) and 210 mg sodium hydro gencarbonate in 1.5 ml THF and 1.5 ml water was stirred under 70 bar CO for 20 hour at 120°C, THF was removed under reduced pressure, 0.5 ml 2M NaOH was added and the suspension was filtered. The clear solution was treated with 0.52 ml hydrochloric acid 25 %, stirred for lh at rt, filtered and the white crystals were dried at 40°C, to obtain 146 mg 2-trifluoromethyl-isonicotinic acid. GC-EI-MS: M 191⁺.

References:

F. HOFFMANN-LA ROCHE AG;HOFFMANN-LA ROCHE INC.;TRUSSARDI, René WO2014/76127, 2014, A1 Location in patent:Page/Page column 11-12

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